Sodium Carbonate → 4,4'-Bis(N,N-bis(t-butoxycarbonylmethyl)aminomethyl)-2,2'-bipyrimidine

HRID 1586936Notes

Reaction equation

HRID 1586936 reaction equation
Cl[CH2:2][C:3]1[CH:8]=[CH:7][N:6]=[C:5]([C:9]2[N:14]=[C:13]([CH2:15]Cl)[CH:12]=[CH:11][N:10]=2)[N:4]=1.[NH:17]([CH2:26][C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:18][C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20].[C:34](=[O:37])([O-:36])[O-].[Na+].[Na+]>C(#N)C>[C:30]([O:29][C:27]([CH2:26][N:17]([CH2:2][C:3]1[CH:8]=[CH:7][N:6]=[C:5]([C:9]2[N:14]=[C:13]([CH2:15][N:17]([CH2:18][C:19]([O:21][C:22]([CH3:25])([CH3:23])[CH3:24])=[O:20])[CH2:26][C:34]([O:36][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:37])[CH:12]=[CH:11][N:10]=2)[N:4]=1)[CH2:18][C:19]([O:21][C:22]([CH3:24])([CH3:25])[CH3:23])=[O:20])=[O:28])([CH3:33])([CH3:32])[CH3:31]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 4393691DI-T-Butyl iminodiacetateHCID 197601294,4'-Bis(chloromethyl)-2,2'-bipyrimidine

Product 1

HCID 197601264,4'-Bis(N,N-bis(t-butoxycarbonylmethyl)aminomethyl)-2,2'-bipyrimidine

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

4,4'-Bis(chloromethyl)-2,2'-bipyrimidine (18.0 mg, 0.0793 mmoles), di-t-butyl iminodiacetate (76.3 mg, 0.31 mmoles), sodium carbonate (210 mg) and acetonitrile (3 ml) were refluxed overnight. The mixture was filtered, the solvent was evaporated and the product was purified by flash chromatography (silica, 0-5% methanol/chloroform).

Workup

  1. filtrationThe mixture was filtered
  2. customthe solvent was evaporated
  3. customthe product was purified by flash chromatography (silica, 0-5% methanol/chloroform)

Sources & evidence

ORD record
ord-3ae7fa321c324cd4a1d2146bfa9d575b
Source dataset
uspto-grants-1993_06
Patent number
US05216134

Reaction notes

Loading…